Water → HCID 59571210, compound
Reaction equation
BrC1C=CC(S([O:11][C@@H:12]2[CH2:51][N:15]3[C:16](=[O:50])[C@@H:17]([NH:36][C:37]([O:39][C@@H:40]4[CH2:44][CH2:43][CH2:42][C@H:41]4[CH2:45][CH2:46][CH2:47][CH:48]=[CH2:49])=[O:38])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH:24][C@@H:25]4[CH2:30][C@@:26]4([C:31]([O:33][CH2:34][CH3:35])=[O:32])[NH:27][C:28](=[O:29])[C@@H:14]3[CH2:13]2)(=O)=O)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].CCO[C:61]([CH3:63])=O.O.[CH3:65][N:66]1[C:70](=O)[CH2:69][CH2:68][CH2:67]1>>[O:50]=[C:16]1[N:15]2[CH2:51][C@H:12]([O:11][C:68]3[C:67]([CH:61]=[CH2:63])=[N:66][C:65]4[C:70]([CH:69]=3)=[CH:14][CH:13]=[CH:12][CH:51]=4)[CH2:13][C@H:14]2[C:28](=[O:29])[NH:27][C@:26]2([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:30][C@H:25]2[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C@@H:17]1[NH:36][C:37]([O:39][C@@H:40]1[CH2:44][CH2:43][CH2:42][C@H:41]1[CH2:45][CH2:46][CH2:47][CH:48]=[CH2:49])=[O:38]Participants
6
Conditions
- Temperature
- 60 °C
Procedure
To a solution of the compound from Step 3 (75 mg, 0.09 mmol) and 2-vnylquinolin-3-ol (16 mg, 0.09 mmol) in NMP (0.2 mL) was added Cs2CO3 (92 mg, 0.28 mmol). The reaction mixture was stirred at 60° C. for 1 hour. The reaction mixture was worked up with EtOAc and water, and the organic was washed with NaHCO3 and brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by silica gel chromatography (gradient elution 5 to 80% EtOAc in hexane). LCMS (M+H)+=727.3.
Workup
- washthe organic was washed with NaHCO3 and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude material was purified by silica gel chromatography (gradient elution 5 to 80% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-eca54942c9ab40588a4ace807d088c59
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08377874B2
Reaction notes
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